Table 3.
Cyclocondensation reactions between benzosuberone (1) and arylhydrazonals 2a–j using Q-tube.a
Entry | Reactants | Ar1 | Ar2 | Product | Yield (%) |
---|---|---|---|---|---|
1 | 1 + 2a | 4-Cl-Ph | 4-Cl-Ph |
![]() |
98 |
2 | 1 + 2b | Ph | 2-F-5-NO2-Ph |
![]() |
94 |
3 | 1+ 2c | 4-Cl-Ph | 2-Cl-5-NO2-Ph |
![]() |
99 |
4 | 1 + 2d | 4-Br-Ph | 2-Cl-5-NO2-Ph |
![]() |
96 |
5 | 1 + 2e | 4-Cl-Ph | 2-F-5-NO2-Ph |
![]() |
97 |
6 | 1 + 2f | 4-NO2-Ph | 2-F-5-NO2-Ph |
![]() |
95 |
7 | 1 + 2g | 4-Br-Ph | 2-F-5-NO2-Ph |
![]() |
96 |
8 | 1 + 2h | 4-Br-Ph | 2,4-diF-Ph |
![]() |
99 |
9 | 1+ 2i | 4-MeO-Ph | 2-F-5-NO2-Ph |
![]() |
91 |
10 | 1 + 2j | C4H3S | 2-F-5-NO2-Ph |
![]() |
93 |
aReaction conditions: a mixture of benzosuberone (1) (5 mmol), arylhydrazonopropanal 2a–j (5 mmol), and NH4OAc (10 mmol) in AcOH (10 ml) was charged in the Q-tube reactor's 35 ml glass tube and heated for 30 min at 165 °C (oil bath).